Phosgene → 5-(1-Methylcyclopropyl)-1,3,4-oxadiazol-2(3H)-one

HRID 1380532Notes

Reaction equation

HRID 1380532 reaction equation
[CH3:1][C:2]1([C:5]([NH:7][NH2:8])=[O:6])[CH2:4][CH2:3]1.[C:9](Cl)(Cl)=[O:10]>C(Cl)Cl>[O:10]=[C:9]1[O:6][C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[N:7][NH:8]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 107491571-Methylcyclopropanecarbohydrazide

Product 1

HCID 127870775-(1-Methylcyclopropyl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

85 gm of 1-methylcyclopropane carboxylic acid hydrazide was added to methylene chloride on a 3-neck 2-liter round bottom flask. The system was first cooled to 0°-5° C. and 590.5 gm of a 12.5% solution of phosgene added dropwise over a period of time. The system was then heated at reflux for 7 hours. The methylene chloride was removed by stripping. The product was washed with petroleum ether and filtered to give 66.6 gm of 5-oxo-2-(1'-methylcyclopropyl)-1,3,4-oxadiazoline as light brown crystals, melting point 68°-70° C.

Workup

  1. temperatureThe system was first cooled to 0°-5° C.
  2. temperatureThe system was then heated
  3. temperatureat reflux for 7 hours
  4. customThe methylene chloride was removed by stripping
  5. washThe product was washed with petroleum ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-de7d6322833c4040896f8278714e7f93
Source dataset
uspto-grants-1986_04
Patent number
US04582828

Reaction notes

Loading…